Into The Unknown

Her fingers clawed at the bedclothes pulling wave-like, elongated ripples into the fabric. Above me she looked like a she-devil. Her eyes rolled back, her jaw raised to expose her sensuous neck, her breath coming in sharp deep pants. This was my woman doing what she enjoys most.

Madelaine was astride me, impaled to the hilt on my cock, with her clitoris rubbing fiercely upon my public bone. In this position she manipulates the angle of my penis to stroke her G spot and uterus, multiplying her pleasure immeasurably.

From experience I knew that her instructions would be explicit, I must knead her breasts forcefully while at the same time pinching her nipples with the thumb and forefinger on each hand. The harder I pinch the nipples, the more intense the spasms of her pussy become as it massages my cock.

Then that magical moment arrives. Initially she wails faintly and then suddenly transforms to a grunting, convulsing wild-thing as her orgasm erupts. The tremors last for several minutes before she flops down onto my chest, still panting from both her orgasm and the physical effort that brought it about.

This position almost always guarantees an orgasm for my lover, but also has the side effect of keeping me aroused without getting me too close to orgasm myself. The obvious benefit of this is that we can keep making love in some other position and tonight I had a new position in mind.

We had spoken years before about anal sex and my lover was clearly not interested. Some years after that I had written a fantasy story about anal sex and submitted it to a website not unlike Literotica. Unfortunately the drafts of the story were still in my computer and she discovered them, quite innocently, while looking for another document.

She raised the issue and we discussed it, with me telling her that I understood that she did not want to participate in such an act, that it was merely a fantasy, and that it was always the forbidden things in life that kept people's interest kindled. I thought that she would be shocked and that she would view me as some kind of pervert.

Imagine my surprise when she said that she would try it if I would be prepared to allow her to insert a dildo of similar size to my cock into my ass, so that I knew what the feeling (good or otherwise) would be like. Basically, if I couldn't take it, then she wouldn't take it.

I accepted the challenge and in the months that followed I used opportunities where she was away from home to "practice" taking it in the ass. I started with a quite small vibrator and over time was able to relax enough to take a vibe the size of my own cock. I learnt a lot about what needs to be done to keep any pain to an absolute minimum and eventually reached a point where it felt good.

When I was confident that I could live up to my end of the bargain, I made my announcement. Unfortunately any further activity of this forbidden nature was curtailed while we had visitors stay with us, my lover became ill for a short while and then we stayed with other people. All of these factors not only ceased my pursuit of the forbidden fruit, but also killed our entire sex-life completely.

Finally everything was coming back into place and having just given Madelaine a satisfying orgasm, it was time to make a move.

I asked my lover if she would suck my cock while inserting the small vibrator into my asshole. She knew where this was heading but agreed enthusiastically. Within minutes I was standing at the edge of the bed as she teased my shaft with feather-like licks and tickled my balls with one hand.

With her other hand she gently but insistently pushed the well lubricated head of the small vibrator into my waiting anus. It met with a slight resistance at the first ring of muscle, but after a short while it entered almost without me even noticing. I joked with my girl that she better not let go of it or the result might be a little embarrassing.

She stopped teasing my cock and took me into her warm, wet, mouth engulfing about half of my length. These exquisite sensations combined with the vibrator tingling my prostate and threatened to make me come all too soon.

I suggested she stop momentarily and replace the small vibe with the next size up. We have several to choose from. The short pause with her mouth away from my rock hard cock while she lubricated the next vibe gave me just the breathing space I needed to compose myself and avoid coming too soon.

The larger vibe eased into my ass, stretching it wider and going in deeper than the previous one. I had to ask her to hold it still for a while as I relaxed and became comfortable with the incredible full feeling that I experienced. After a few minutes I took control and began to move up and down the vibe as my lover held the end still.

She had resumed her ministrations to my penis and the warm wave of pleasure that swept over me was unlike anything I had felt before. I did not want to orgasm, but I did want to keep the vibrator in for as long as I could to prove to my girl that it could be done.

Finally I suggested that I be impaled with the vibrator closest in size to my own cock. The size difference was not that great and it slipped in with no resistance. This vibrator was one filled with beads that allow the shaft to twist and rotate while massaging the walls of the pussy, or in this case ass, of the receiver.

I have to admit to fleetingly wondering if perhaps I was a latent homosexual as I was really enjoying this. Of course I'm not homosexual and have never had any feelings toward other men, but I can now appreciate how they get off on the feeling of being impaled by another man.

I was getting dangerously close to orgasm now and asked my lover to stop, explaining that I wanted to keep my climax for when I was deep inside her. I could sense that she was a little uneasy, so I promised that I would stop at any time she asked.

I positioned her on her back and had her draw her knees toward her chest. I licked her pussy gently as I applied liberal amounts of lube on her virgin hole. I traced lazy circles around the rim of her ass using my index finger. I made no attempt to enter, preferring to let her get used to the new sensations.

I rolled her over onto her stomach and began to massage her lower back and buttocks with some scented oil. After some time I handed her a vibrator, set to low speed, and had her place it against her clitoris. I allowed her some time to build some pleasure before I again began to rub her opening. I then gently inserted a single finger just far enough to push against her inner muscle. After a short while I withdrew and inserted the opening of the lubricant tube in the place of my finger.

I squeezed a generous amount of lubricant into her passage and the reinserted my finger, rotating it slightly as I pressed gently against the expected resistance. Soon I could feel the small jerking spasms as she endeavoured to relax and allow further entry.

After a few more minutes the end of my finger passed through her formerly unpenetrated barrier. I knew from experience that this was a time to take extra care, as my lover would be experiencing an urge to bear down as though using her bowels. I continued only after I sensed her breathing resuming its regular rhythm.

With gentle inward movement I eventually had my second knuckle inside her. At this time I rolled her onto her back and began to once again caress her pussy with my tongue. She kept the vibrator at her pearl bud, wiping it across in small circles. I withdrew my finger and added more lubricant to her anus. The smallest vibrator was prepared for use and rested against her opening.

I asked her if she was happy to continue. She said nothing but nodded in the affirmative. Slowly but insistently I pushed the little buzzing cylinder into the tight opening, feeling all the while for the ring of muscle that would attempt to prevent its invasion. Once reaching the obstacle I waited, just nudging the vibe inward a very small amount and then letting it push back out the same amount.

Each inward thrust was minutely deeper than the last until without any pain, it slid quickly past this major hurdle and glided effortlessly further inside my panting lover. Again I lapped at her pussy, moving the other vibrator out of the way so that I could lavish attention to her clit. Several minutes later I began to make deliberate, gentle strokes of the vibrator in her ass. I gently eased it in a circular motion to stretch and relax her muscles.

My girl said that she wasn't sure if she could take a bigger size so I told her to relax for a while longer and enjoy the pussy show. I removed the smallest vibrator and oiled up the next size. This was placed at her entrance and used to rim her at first and then I began to insert it. The resistance was far greater on this occasion and I applied firm pressure against her clitoris with my tongue, hoping to arouse her sufficiently to overcome any discomfort that she may be feeling.

Steadily I insistently inserted the vibrating gold cylinder, asking my girl to bear down on it slightly to force her sphincter muscles to open over it. This worked and without warning the resistance was over and the inward motion commenced. It was clear that my lover was experiencing some discomfort now and I offered to stop. At first she agreed but as I began to withdraw she stopped me and forced herself over the invader.

She kept quite still for some time after the vibe reached its maximum depth, urging me to bring her to orgasm with my willing mouth. This I did with relish. With my spare hand I began to masturbate, hoping to keep myself at a stage where I would be able to come soon after entering her and before my beautiful lover was no longer able to be fucked in her beautiful ass.

Then came the moment I had be waiting for. I was asked to remove the vibrator from her ass and lube my cock. Without rushing I removed the throbbing artificial cock and applied copious lubricant to my penis. My lover told me to come as quickly as I could because she wasn't sure if she could handle the invasion for long.

Without any further hesitation I pushed her legs further up against her chest and kneeled so that my glans touch the forbidden entrance. I began to lean forward with gentle pressure but was stopped by my girl.

"Let me control this" she said. She then wiggled her buttocks in small circles, massaging my helmet as she did so. Ever so slowly I felt the outer ring open and slide over me, until the tip of my penis pushed against the inner ring. This was to be the moment of truth.

I reached down and flicked my finger over her pearl bud, trying to again distract her as she prepared for the final assault. I felt her bear down on me, the strong ring of muscle opening to admit the head of my cock. Suddenly I was through and her sphincter instinctively tightened again as the widest part of my helmet passed through. The grip on my shaft was incredible and the heat I felt was unlike anything that I had experienced in her pussy.

My darling was perspiring and I offered to withdraw but she just shook her head and drove down on my cock, sliding another two inches in. She paused briefly and then pushed again. My belly was so close to hers now, that I could no longer stroke her clitty. I began to pull back for my first stroke but was ordered to stay still.

"Now" she said and with that I began to more in and out very slowly and gently. Soon she was thrusting her pelvis to match my movements. The incredible tightness was milking me, creating sensations that built up much more rapidly than I experience during regular intercourse. Within a minute I felt the unmistakable boiling in my loins as I felt the come rising from deep within me. I drove home, placing my entire length within her as I began to erupt with overwhelming spasms of ejaculate.

My cock slowly shrank and withdrew naturally from my beautiful lady, exiting with a wet plopping sound that was followed by a stream of glistening cum juices. We had crossed the bridge that for so long seemed to be insurmountable. Who knows whether this will happen again or if it may lead us to try other things, but one thing is for sure, I am one happy rooster.